Dimethylformamide → Methyl 5'-chloro-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-(trifluoromethylsulfonyloxy)benzoate 66.61 (0.100 g, 0.3 mmol) in DMF (4 mL) at 23° C. was added 5-chloro-2-fluorophenylboronic acid (0.07 g, 0.4 mmol) (commercially available from Aldrich), potassium carbonate (0.1 g, 0.8 mmol), followed by tetrakis(triphenylphosphine)palladium (0.03 g, 0.03 mmol). The mixture was heated to 90° C. and stirring was continued for 23 hours. The reaction was then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was purified on silica gel (0-10% EtOAc in hexanes) to yield 78.9A as a colorless oil (0.082 g, 86% yield).

Provenance & Evidence